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If using Gmail, or Google as your SMTP provider, please select TLS for security and use port 587. Note also that by default Google may not allow you to set a send from an address set in your email templates that if it is different than the user you authenticate with via SMTP. In order to send from a different address, you must create an alias in Gmail under Settings > Settings > Accounts where . Where it says "Send mail as:" add an address and check the box that says "Treat as an alias.".